PRODUCTS

VERATRALDEHYDE

Veratraldehyde is used as an antifungal agent.
Veratraldehyde is used as a flavorant and odorant.
Veratraldehyde is used in pharmaceutical industry to synthesize methyldopa.

CAS Number: 120-14-9
IUPAC Name: 3,4-dimethoxybenzaldehyde
MDL Number: MFCD00003363
Chemical formula: C9H10O3
Molar mass: 166.176 g·mol−1

SYNONYMS:
3,4-Dimethoxybenzenecarbaldehyde, Methylvanillin, Veratric aldehyde, Veratral, Veratryl aldehyde, Veratrum aldehyde, Vanillin methyl ether, benzaldehyde, 3,4-dimethoxy-, 3,4- dimethoxy benzaldehyde, 3,4- dimethoxy-benzaldehyde, 3,4- dimethoxybenzaldehyde, 3,4- dimethoxybenzene carbinol, dimethyl ether protocatechualdehyde, 3,4- dimethyloxybenzaldehyde, methyl vanillin, protocatechualdehyde dimethyl ether, protocatechuec aldehyde dimethyl ether, protocatechuic aldehyde dimethyl ether, vanillin methyl ether, vanillyl methyl ether, veratraldehyde FCC, veratraldehyde flakes, veratric aldehyde, p- veratric aldehyde, para- veratric aldehyde, veratrum aldehyde, veratryl aldehyde, veratryl aldehyde powder, veratrylaldehyde (chunks), veratrylaldehyde congealed solid, veratrylaldehyde powder, 3,4-Dimethoxybenzaldehyde, VERATRALDEHYDE, 120-14-9, Veratric aldehyde, Benzaldehyde, 3,4-dimethoxy-, Vanillin methyl ether, Veratrum aldehyde, Veratryl aldehyde, Veratral, p-Veratric aldehyde, 4-O-Methylvanillin, 3,4-Dimethoxybenzenecarbonal, Protocatechualdehyde dimethyl ether, Protocatechuic aldehyde dimethyl ether, FEMA No. 3109, UI88P68JZD, DTXSID7026285, NSC-8500, NSC-24521, DTXCID406285, CHEBI:17098, RefChem:193958, 204-373-2, Methylvanillin, 3,4-Dimethoxy benzaldehyde, MFCD00003363, 3,4-DIMETHOXY-BENZALDEHYDE, Protocatechuecaldehyde dimethyl ether, NSC 24521, Verapamil EP Impurity G, 3, 4-Dimethoxybenzaldehyde, Methyl vanillin, Benzaldehyde,4-dimethoxy-, WLN: VHR CO1 DO1, CAS-120-14-9, CCRIS 6285, EINECS 204-373-2, UNII-UI88P68JZD, BRN 0473899, veratrumald, ratryl aldehyde, Veratrumaldehyde, AI3-08099, FEMA 3109, 3,4-dimethoxy, 3,4dimethoxybenzaldehyde, 3,4-dimethoxybenzaldeyde, 3,4 dimethoxybenzaldehyde, 3,4-dimethoxybenzaidehyde, 4,3-dimethoxybenzaldehyde, 4,5-dimethoxybenzaldehyde, bmse010220, VERATRALDEHYDE [MI], VERATRALDEHYDE [FCC], SCHEMBL25202, SCHEMBL56335, VERATRALDEHYDE [FHFI], Veratraldehyde, >=98%, FG, orb1301612, CHEMBL1088937, SCHEMBL19716028, SCHEMBL29364994, MSK3363, NSC8500, 3,4-Dimethoxybenzaldehyde, 99%, BB_NC-02052, HY-N1096, NSC24521, Tox21_201566, Tox21_303074, BBL010373, EBC-03268, MSK3363-100M, s3214, SBB040236, STK188425, AKOS000118989, MSK3363-1000M, CS-W019906, Dimethoxy-Benzaldehyde-O-Methylvanillin, FD54842, NCGC00091642-01, NCGC00091642-02, NCGC00091642-03, NCGC00257217-01, NCGC00259115-01, AC-10201, AC-34441, AS-11996, SY004136, Benzaldehyde, 3,4-dimethoxy-veratraldehyde, Veratraldehyde (3,4-Dimethoxybenzaldehyde), DB-014213, D0507, NS00013328, ST45169641, EN300-16145, C02201, Methylvanillin Solution in Methanol, 100ug/mL, Methylvanillin Solution in Methanol, 1000ug/mL, AH-034/32845024, F078760, Q414395, Z53837671, F2190-0618, VERAPAMIL HYDROCHLORIDE IMPURITY G [EP IMPURITY], InChI=1/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H, veratraldehyde protocatechuic aldehyde dimethyl ether protocatechualdehyde dimethyl ether veratrum aldehyde protocatechuecaldehyde dimethyl ether, 3,4-DIMETHOXYBENZALDEHYDE, 3,4-DIMETHOXYANILINE, Benzaldehyde, 3,4-dimethoxy-, 204-373-2, VERATRYL ALDEHYDE, METHYL VANILLIN, Methyl vanilline, Veratral, VERATRIC ALDEHYDE, 4-O-Methylvanillin, 3,4-Dimethoxybenzaldehyde, Methylvanillin, NSC 24521, NSC 8500, Vanillin methyl ether, Veratraldehyde, Vanillin methyl ether, Methylvanillin, 3,4-Dimethoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 3,4-Dimethoxybenzaldehyde, 3,4-Dimethoxybenzaldehyde, Veratraldehyde, Veratric aldehyde, 3,4- dimethoxybenzaldehyde, 3,4- dimethoxybenzene carbinol, dimethyl ether protocatechualdehyde, methyl vanillin, protocatechualdehyde dimethyl ether, protocatechuec aldehyde dimethyl ether, protocatechuic aldehyde dimethyl ether, vanillin methyl ether, veratric aldehyde, para- veratric aldehyde, veratrum aldehyde, veratryl aldehyde, Apple, Veratraldehyde, Berje, Veratraldehyde, Hofmen, Veratraldehyde, 99pc, Moellhausen, veratraldehyde 98pc min. nature identical kosher, Penta, veratrylaldehyde powder, Penta, veratrylaldehyde chunks, Polarome, VERATRALDEHYDE FCC

Veratraldehyde is an organic compound that is widely used as a flavorant and odorant.
Veratraldehyde is structurally related to benzaldehyde.
Veratraldehyde is popular commercially because of its pleasant woody fragrance.

Veratraldehyde is derivative of vanillin, from which it is prepared by methylation.
Veratraldehyde is a crystalline aroma chemical with a soft powdery vanilla custard quality.

Veratraldehyde is a really good alternative to vanillin (though it suffers from the same discolouration problems in soaps) or can be used to add nuance and interest to the same.
Veratraldehyde is a versatile aromatic aldehyde known for its distinctive properties and applications in various industries.

With its chemical structure featuring two methoxy groups, Veratraldehyde exhibits excellent solubility in organic solvents, making it an ideal candidate for use in the synthesis of fragrances, flavoring agents, and pharmaceuticals.
Veratraldehyde is particularly valued in the production of vanillin and other aromatic compounds, which are essential in the food and cosmetic industries.

Additionally, Veratraldehyde serves as a valuable intermediate in organic synthesis, enabling researchers to explore innovative pathways in chemical reactions.
Veratraldehyde is a crystalline solid with a woody, vanillalike odor.

Veratraldehyde can be prepared by methylation of vanillin or by methylation of vanillin and dimethyl sulfate.
Veratraldehyde is also found in peppermint, ginger, raspberry, and other fruits.
Veratraldehyde has a powdery balsamic odour reminiscent of vanilla and benzoin.

The odour is not particularly strong, but, for Veratraldehyde is a solid: making a solution in DPG, TEC or IPM can be useful.
Making a stable 10% solution is possible with all these solvents, in TEC and DPG 25% is possible as well.
Keep Veratraldehyde cool, dry, dark and out of reach of children.

Veratraldehyde is a significant organic compound widely utilized in the fragrance and flavor industry.
Veratraldehyde's synthesis involves the oxidation of vanillin using potassium dichromate and Lewis acids under solid phase conditions, which provides better control and yield.

Veratraldehyde finds applications as a reactant in the production of pharmaceuticals, agrochemicals, and polymer additives.
Veratraldehyde serves as a precursor for important chemicals like vanillin, veratric acid, and methoxybenzaldehydes.

Veratraldehyde is also used as a catalyst in various organic synthesis reactions, facilitating the formation of important compounds with high selectivity and efficiency.
Overall, veratraldehyde is a versatile compound with diverse applications in the chemical industry.

Veratraldehyde is Needles or chunky light peach powder.
Veratraldehyde has an odor of vanilla beans.
Veratraldehyde is insoluble in water.

Veratraldehyde is soluble in water.
Veratraldehyde is freely soluble in alcohol and ether.
Veratraldehyde is incompatible with oxidizing agents.

Veratraldehyde is an organic compound that is widely used as a flavorant and odorant.
Veratraldehyde is structurally related to benzaldehyde.
Veratraldehyde is a dimethoxybenzene that is benzaldehyde substituted by methoxy groups at positions 3 and 4.

Veratraldehyde is found in peppermint, ginger, raspberry, and other fruits.
Veratraldehyde is a crystalline aroma chemical with a soft powdery vanilla custard quality.
In the age of the gourmand, Veratraldehyde absolutely cannot go unnoticed and we highly recommend it for all perfumers.

Veratraldehyde presents a sweet, balsamic, vanilla-like aroma with warm creamy facets and subtle spicy undertones.
Veratraldehyde (3,4-dimethoxybenzaldehyde) is an organic compound with the formula (CH3O)2C6H3CHO.
Several isomers are known.

Veratraldehyde is structurally related to benzaldehyde, with two methoxy groups.
Veratraldehyde is popular commercially because of its pleasant woody fragrance.
Veratraldehyde is derivative of vanillin, from which it is prepared by methylation.

Veratraldehyde can be obtained by chemical degradation of lignin.
Veratraldehyde appears as needles or chunky light peach powder.
Veratraldehyde has an odor of vanilla beans.

Veratraldehyde is a dimethoxybenzene that is benzaldehyde substituted by methoxy groups at positions 3 and 4.
Veratraldehyde is found in peppermint, ginger, raspberry, and other fruits.
Veratraldehyde has a role as an antifungal agent.

Veratraldehyde is a member of benzaldehydes and a dimethoxybenzene.
Veratraldehyde has been reported in Wisteria floribunda, Zingiber montanum, and other organisms with data available.
Veratraldehyde is a dimethoxybenzene that is benzaldehyde substituted by methoxy groups at positions 3 and 4.

Veratraldehyde is found in peppermint, ginger, raspberry, and other fruits.
Veratraldehyde has a role as an antifungal agent.
Veratraldehyde is a member of benzaldehydes and a dimethoxybenzene.

Veratraldehyde, chemically known as 3,4-dimethoxybenzaldehyde, is an organic compound with the molecular formula C₉H₁₀O₃.
Veratraldehyde is a white crystalline solid that exhibits a pleasant vanilla-like odor.

Veratraldehyde serves primarily as a flavoring agent in food products and a key ingredient in perfumery, where it imparts warmth and depth similar to but more nuanced than vanillin.
Approved by regulatory bodies such as the FDA (21 CFR 172.515) and FEMA (No. 3109), it is used to enhance floral and vanilla profiles in various consumables.

Veratraldehyde occurs naturally in several plants, including peppermint (Mentha piperita), ginger (Zingiber officinale), raspberry (Rubus idaeus), and other fruits, contributing to their characteristic aromas.
In human metabolism, Veratraldehyde acts as a metabolite and is found in cellular locations such as the cytoplasm and extracellular spaces.

Physically, Veratraldehyde has a melting point of 42–45 °C and a boiling point of 281 °C at standard pressure, with low solubility in water (<1 mg/mL at 25 °C) but good solubility in ethanol and oils.
Veratraldehyde's structure features a benzene ring substituted with an aldehyde group at position 1 and methoxy groups at positions 3 and 4, making it a derivative of benzaldehyde and a member of the dimethoxybenzene class.

In industrial applications, veratraldehyde is synthesized for use in oriental-type fragrances and as a food additive, where it provides a custard-like, powdery quality with notes of cherry, creamy woodiness, and sweetness.

Safety assessments, including those by JECFA in 2001, indicate no safety concerns at typical flavoring intake levels, though Veratraldehyde is classified as harmful if swallowed (GHS H302) and can irritate skin, eyes, and respiratory tracts.
Veratraldehyde is also recognized for potential roles as an antifungal agent and in pesticide formulations as an inert fragrance component.

USES and APPLICATIONS of VERATRALDEHYDE:
Typical use is in oriental accords, but also in sweet florals.
You usually use between 0,1% and 10% of Veratraldehyde in the fragrance composition.
Veratraldehyde combines well with other balsamic fragrances, but also with, for example, many wood fragrances.

Veratraldehyde is less painfully sweet than vanillin and ethyl vanillin and can be used more subtly.
In perfumes, Veratraldehyde is mainly a base note and is stable in most products, including soap, although it can cause product discolouration.
Veratraldehyde was used in the preparation of 4-chloromethyl-2-(dimethoxyphenyl)-1,3-dioxolane.

Veratraldehyde was used in the synthesis of (+)-lithospermic acid, having anti-HIV activity.
Veratraldehyde forms 1:1 inclusion complexes with cyclodextrins.
Veratraldehyde reacts with 3-acetyl-2,5-dimethythiophene to yield chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one.

Veratraldehyde is used as an antifungal agent.
Veratraldehyde is used as a flavorant and odorant.
Veratraldehyde is used in pharmaceutical industry to synthesize methyldopa.

Veratraldehyde is used in the production of veterinary drug sulfonamide synergist.
Veratraldehyde is used for the synthesis of antibiotic drugs.
Veratraldehyde is used in oriental and warm, woody fragrances, as well as in flavor compositions for vanilla notes.

Veratraldehyde is a fragrance for use in perfume, cosmetics, soap and air fresheners.
In the realm of research, Veratraldehyde is utilized in the development of advanced materials and as a reagent in various chemical transformations.

Its unique properties allow for the creation of complex molecules, making Veratraldehyde a favored choice among chemists and industry professionals.
Veratraldehyde's stability and reactivity provide significant advantages over similar aldehydes, enhancing its appeal for applications in both academic and industrial settings.

Whether in the formulation of perfumes or the synthesis of novel compounds, Veratraldehyde stands out as a crucial ingredient that drives innovation.
Uses: Veratraldehyde creates sophisticated vanilla and heliotrope effects while enhancing oriental compositions with refined balsamic qualities.

Veratraldehyde was used in the preparation of 4-chloromethyl-2-(dimethoxyphenyl)-1,3-dioxolane.
Veratraldehyde was used in the synthesis of (+)-lithospermic acid, having anti-HIV activity.
Veratraldehyde forms 1:1 inclusion complexes with cyclodextrins.

Veratraldehyde is used in the synthesis of (+)-lithospermic acid, having anti-HIV activity.
Veratraldehyde is a really good alternative to vanillin (though it suffers from the same discolouration problems in soaps) or can be used to add nuance and interest to the same.

Veratraldehyde is widely used as a flavorant and odorant.
Veratraldehyde can be used as an intermediate in the synthesis of some pharmaceutical drugs including amiquinsin, hoquizil, piquizil, prazosin, quinazoline, tiapamil, toborinone, verazide, and vetrabutine.

Veratraldehyde is the intermediate of organic synthesis.
In pharmaceutical industry, Veratraldehyde is used to synthesize methamphetamine and also used in the production of veterinary drug sulfonamide synergist.

Adding 0.02% (weight) of this veterinary drug into feed can increase the efficiency of the iodine drug synergistic added in feed, which can prevent and control the poultry bacterial infection.
Veratraldehyde is used as pharmaceutical intermediate and mainly used for antibiotic drug synthesis.

Veratraldehyde reacts with 3-acetyl-2,5-dimethythiophene to yield chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one.
Veratraldehyde serves as a key intermediate in the synthesis of certain dyes, notably reacting with 3-acetyl-2,5-dimethylthiophene to form the chalcone dye (2E)-3-(3,4-dimethoxyphenyl)-1-(2,5-dimethyl-3-thienyl)-2-propen-1-one, which finds application in specialized coloring processes.

In polymer chemistry, Veratraldehyde contributes to the production of high-performance resins and acts as a chemical intermediate in specialty coatings and adhesives, enhancing material durability and functionality.
A notable application involves Veratraldehyde's derivatization from lignin, a renewable biomass source, to create advanced materials such as nanofibrous hyper-cross-linked polymers.

These polymers, synthesized via triarylimidazole monomers from veratraldehyde, exhibit high adsorption capacity for cationic organic pollutants, supporting sustainable wastewater treatment and environmental remediation efforts.
In agricultural chemicals, veratraldehyde is utilized as a precursor in the formulation of pesticides and herbicides, aiding in the development of effective crop protection agents.

Additionally, Veratraldehyde forms 1:1 inclusion complexes with cyclodextrins, which improve the solubility and stability of various industrial compounds, facilitating their incorporation into formulations requiring enhanced delivery or controlled release.

Historically, veratraldehyde has been employed as a temporary consolidant for preserving underwater cultural heritage relics, where its denser-than-water properties allow penetration into porous artifacts for solidification without altering their original structure.
This application, documented in early 21st-century conservation studies, highlights Veratraldehyde's role in material science for heritage protection.

-Applications of Veratraldehyde in organic synthesis:
Reactant
Veratraldehyde has various applications as a reactant in the chemical industry.

Veratraldehyde is used in the production of pharmaceuticals, agrochemicals, and polymer additives.
Veratraldehyde serves as a precursor for many important chemicals, including vanillin, veratric acid, methoxyphenols, and methoxybenzaldehydes.

These compounds are widely used in the food, pharmaceutical, and cosmetic industries as well as in biotechnology and material science.
Additionally, Veratraldehyde is used in the synthesis of novel nonpeptide antagonists of endothelin I, which have proven to be useful in treating various medical conditions such as hypertension, myocardial infarction, asthma, preeclampsia, cancer, stroke, and diabetes.

These compounds act by blocking the effects of endothelin I, a hormone that plays a crucial role in regulating blood pressure, vascular tone, and cell proliferation.

In conclusion, Veratraldehyde is a versatile and valuable compound with many applications in the chemical industry.
Veratraldehyde's use as a reactant allows for the production of various important chemicals, while its involvement in the synthesis of novel pharmaceuticals makes it an essential component in the development of new drugs for various medical conditions.

-Catalyst uses of Veratraldehyde:
Veratraldehyde has various applications as a catalyst in organic synthesis.
Veratraldehyde is used as a reactant to form ate complexes, which act as efficient catalysts for a wide range of reactions, including β-hydride transfer reactions, cycloadditions, and cross-coupling reactions.

The ate complexes of Veratraldehyde are highly reactive and can selectively catalyze various transformations.
For instance, they can be used to convert 3-alkyl-3-borabicyclo[3.3.1]nonanes and 3-alkyl-3-borabicyclo[3.3.1]non-6-enes into 5-substituted 3-methylenecyclohex-1-ylmethyl(dialkyl)boranes.

These compounds can then be oxidized to form 3-substituted 1-methylene-5-hydroxymethylcyclohexanes.
The catalyst can also be used in the synthesis of 1,3-di- and 1,3,5-trimethylene derivatives of the cyclohexane series by reacting cycloalkylmethyl(dialkyl)boranes with aromatic aldehydes.

In addition, the Veratraldehyde-based catalyst can be used in the reaction with RLi (R = Me, Bu) to form intermediates, which can be further reacted with AcCl to give desired products, such as IV and V.
The methylene analog gives VI.

Overall, Veratraldehyde is a valuable and versatile catalyst in organic synthesis, facilitating the formation of various important compounds with high selectivity and efficiency.

-In Flavors and Fragrances use of Veratraldehyde:
Veratraldehyde contributes vanilla-like and woody notes to various food products, particularly in bakery items, beverages, and confectionery, where it enhances creamy and nutty profiles.

Veratraldehyde is commonly employed in imitation vanilla formulations, butterscotch flavors, and fruit complexes at typical concentrations of 10 to 30 ppm in finished products.
As a recognized flavoring agent, veratraldehyde holds FEMA GRAS status under number 3109, affirming its safety for use in food applications when adhering to established guidelines.

In the fragrance industry, veratraldehyde serves as a versatile ingredient in perfumes, imparting oriental and woody accords with greater warmth and depth compared to vanillin.
Veratraldehyde is often incorporated into woody-musky bases and oriental compositions at average concentrations of 0.1% to 0.23% in perfume compounds, contributing to notes of cherry, cream, heliotrope, and vanilla.

Its sensory profile features a pleasant, balsamic-vanilla aroma with creamy, powdery, and subtle fruity undertones, making Veratraldehyde suitable for enhancing sophisticated blends.
Commercially, veratraldehyde is a key component in synthetic vanilla extracts and essential oil blends, supporting the production of flavored goods and scented products.

Veratraldehyde functions as an effective heliotropin replacer in fragrance formulations and is widely utilized by suppliers for its stability and organoleptic qualities in both flavor and perfume markets.

-In Pharmaceutical Synthesis use of Veratraldehyde:
Veratraldehyde serves as a key intermediate in the synthesis of several pharmaceutical compounds, particularly those featuring dimethoxy-substituted aromatic scaffolds.

Veratraldehyde is employed in the production of antihypertensive agents like prazosin, as well as calcium channel blockers such as tiapamil, and other drugs including amiquinsin, hoquizil, piquizil, quinazoline derivatives, toborinone, verazide, and vetrabutine.
In these syntheses, veratraldehyde often participates in condensation reactions to form Schiff bases or undergoes reductions to build core drug structures.

For instance, in the traditional multi-step synthesis of prazosin, veratraldehyde is used to construct the 6,7-dimethoxyquinazoline ring system through initial formylation and cyclization steps, though modern routes aim to improve yields by avoiding this lengthy pathway.
The dimethoxyquinazoline core derived from veratraldehyde is then modified with piperazine derivatives in subsequent steps of prazosin production.

Veratraldehyde has been incorporated into FDA-approved manufacturing processes for drugs like prazosin, an alpha-1 blocker for hypertension, but it itself lacks direct therapeutic applications and functions solely as a synthetic building block.
In research contexts, Veratraldehyde contributes to the development of anti-HIV compounds; notably, it undergoes aldol condensation in one strategy for synthesizing (+)-lithospermic acid, a natural product derivative with demonstrated anti-HIV activity.

PROPERTIES of VERATRALDEHYDE:
Veratraldehyde is an almost white to beige solid at room temperature.
We deliver Veratraldehyde in powder, flakes or lumps, this can be different per batch.
The purity is at least 99% and Veratraldehyde has a long shelf life.
Veratraldehyde occurs in nature, but for use as fragrance the synthetic version is used.

PREPARATION of VERATRALDEHYDE:
Veratraldehyde can be derived from the reaction of 3-methoxy-4-hydroxybenzaldehyde (vanillin) and dimethyl sulfate, or derived from the methylation of dimethyl sulfate with vanillin in alkaline conditions.

CHEMICAL PROPERTIES of VERATRALDEHYDE:
Veratraldehyde is an off-white crystalline solid
Veratraldehyde is a crystalline solid (mp 44.5–45°C) with a woody, vanillalike odor.

Veratraldehyde can be prepared by methylation of vanillin.
Veratraldehyde is used in oriental and warm, woody fragrances, as well as in flavor compositions for vanilla notes.

Veratraldehyde is an intermediate in, for example, the synthesis of pharmaceuticals.
Veratraldehyde has a very sweet, woody, vanilla-like odor with a warm, sweet, vanilla-like taste.
Veratraldehyde gets oxidized in air to odorless veratric acid.

Veratraldehyde is a white to brown or blue-gray needle crystal (crystallization in ether); sweet woody fragrance, fragrant grass aroma and strong flavor of vanilla blue; oxidized into odorless 3,4-dimethoxybenzoic acid (veratric acid) in the air; melting point 43~45℃; insoluble in cold water; soluble in hot water, ethanol and oil.

OCCURRENCE of VERATRALDEHYDE:
Reported among the constituents of the essential oils of Cymbopogon javanensis and Eryngium poterium.
Also reported found in raspberry, ginger, peppermint oil, Bourbon vanilla and mastic gum oil.

PREPARATION of VERATRALDEHYDE:
Prepared from vanillin by methylation of vanillin with dimethylsulfate under mildly alkaline conditions.

AROMA THRESHOLD VALUES of VERATRALDEHYDE:
Aroma characteristics at 1.0%: phenolic, sweet vanilla, powdery, slightly woody with a candy and cocoa creaminess.

TASTE THRESHOLD VALUES of VERATRALDEHYDE:
Taste characteristics at 50 ppm: phenolic, vanilla, sweet powdery cocoa, creamy, cherry-like with phenolic and balsamic nuances.

IDENTIFIERS of VERATRALDEHYDE:
Veratraldehyde is assigned several standardized international identifiers that facilitate its identification, retrieval, and regulatory tracking across chemical databases and agencies.
These codes ensure unambiguous reference in scientific literature, safety assessments, and commercial applications.

The Chemical Abstracts Service (CAS) Registry Number for veratraldehyde is 120-14-9, a unique numeric identifier assigned by the American Chemical Society's Chemical Abstracts Service to distinguish chemical substances based on their molecular structure, regardless of names or properties.

In PubChem, veratraldehyde has the Compound ID (CID) 8419; PubChem, maintained by the National Center for Biotechnology Information (NCBI), serves as a comprehensive repository of chemical information, including structures, biological activities, and safety data to support research in chemistry, biology, and medicine.

The ChEBI identifier is CHEBI:17098; ChEBI, curated by the European Bioinformatics Institute (EMBL-EBI), is an ontology-based dictionary focused on small chemical compounds of biological interest, providing classifications and roles in metabolic pathways.

Veratraldehyde's ChEMBL ID is CHEMBL1088937; ChEMBL, also from EMBL-EBI, is a manually curated database of bioactive molecules with drug-like properties, emphasizing compound-target interactions for drug discovery and pharmacology research.
The ChemSpider ID is 21106008; ChemSpider, operated by the Royal Society of Chemistry, is a free chemical structure database aggregating data from numerous sources to enable structure-based searches and property predictions.

For regulatory purposes in the European Union, the ECHA InfoCard number is 100.003.976; the European Chemicals Agency (ECHA) uses this to summarize key substance information from the REACH registration dossier, including hazards, uses, and environmental data for compliance and risk management.

The Unique Ingredient Identifier (UNII) is UI88P68JZD, assigned by the U.S. Food and Drug Administration (FDA) through its Global Substance Registration System (GSRS); UNII codes provide a standardized way to identify active and inactive ingredients in drugs, foods, and cosmetics for regulatory tracking and pharmacovigilance.

In the U.S. Environmental Protection Agency's (EPA) CompTox Dashboard, veratraldehyde is listed as DTXSID7026285; this platform integrates toxicity, exposure, and chemical data to support environmental risk assessment, screening, and prioritization of substances under programs like TSCA.

PHYSICAL AND CHEMICAL PROPERTIES of VERATRALDEHYDE:
*Appearance and Physical Constants
Veratraldehyde appears as peach-colored crystals, colorless to pale yellow lumps, or a fused solid, often described as needles or a chunky light peach powder in pure form.

Veratraldehyde exhibits a pleasant woody fragrance with sweet vanilla-like notes, reminiscent of vanilla beans, which enhances its appeal in fragrance applications.
Under standard conditions of 25 °C and 100 kPa, veratraldehyde is a solid with a density of 1.114 g/mL.
Veratraldehyde's melting point ranges from 40 to 43 °C (104 to 109 °F; 313 to 316 K), and the boiling point is 281 °C (538 °F; 554 K).

*Solubility and Stability
Veratraldehyde exhibits low solubility in water, with reported values of less than 1 mg/mL at 72°F (22°C), though it is insoluble in cold water but soluble in hot water.
Veratraldehyde is readily soluble in organic solvents such as ethanol, ether, chloroform, and oils.

Under normal conditions, veratraldehyde is chemically stable, but it is air-sensitive and can oxidize to veratric acid (3,4-dimethoxybenzoic acid) upon prolonged exposure to air, light, or strong oxidizing agents; this autoxidation process is catalyzed by transition metal salts and activated by light.

For optimal preservation, veratraldehyde should be stored in a cool, dry place, preferably refrigerated, in tightly closed containers away from light, ignition sources, and incompatible materials to prevent degradation.

REACTIVITY AND DERIVATIVES of VERATRALDEHYDE:
Veratraldehyde, as an aromatic aldehyde, exhibits typical reactivity associated with the formyl group, including susceptibility to oxidation by strong oxidizing agents to form veratric acid (3,4-dimethoxybenzoic acid).
This oxidation can be catalyzed under controlled conditions, such as air oxidation at 130 °C and elevated pressure, yielding veratric acid as the primary product.

Additionally, due to the absence of alpha hydrogens, veratraldehyde undergoes the Cannizzaro reaction in the presence of strong bases, leading to a disproportionation product mixture of veratryl alcohol and veratric acid.
Veratraldehyde also participates in aldol condensation reactions, forming beta-hydroxy carbonyl compounds or alpha,beta-unsaturated carbonyls with enolizable carbonyl partners, as exemplified by its reaction with acetophenone derivatives to produce chalcones.

The methoxy groups at the 3 and 4 positions of the benzene ring act as strong ortho-para directors, influencing electrophilic aromatic substitution reactions to favor positions 5 and 6 relative to the aldehyde group, which is a meta director but weaker in activating effect.
This directing influence enhances reactivity toward electrophiles like halogens or nitrating agents at the ortho positions to the methoxy substituents.

(Note: General principle from organic chemistry texts; specific to veratraldehyde derivatives in synthesis literature.)
Common derivatives include veratryl alcohol, obtained via reduction of the aldehyde group using sodium borohydride in methanol, providing a key intermediate for further synthetic transformations.

Veratric acid, the oxidation product, serves as a precursor in pharmaceutical and material syntheses.
Spectroscopic characterization confirms the aldehyde functionality, with infrared (IR) spectroscopy showing a characteristic C=O stretch at approximately 1690-1700 cm⁻¹ and nuclear magnetic resonance (NMR) displaying the aldehyde proton at around 9.8 ppm in CDCl₃.
Veratraldehyde is incompatible with strong oxidizers, potentially generating heat, flammable hydrogen gas, or toxic fumes during reactions, necessitating careful handling to avoid hazardous exothermic processes.

INDUSTRIAL PROCESSES of VERATRALDEHYDE:
Veratraldehyde is primarily produced industrially through the methylation of vanillin, a process scaled up using heterogeneous catalysts to enhance efficiency and reduce environmental impact compared to traditional homogeneous methods.

In this approach, vanillin is reacted with dimethyl carbonate (DMC) as the methylating agent in the presence of a potassium-promoted lanthanum-magnesium mixed oxide catalyst, achieving up to 98% conversion and 95% selectivity at 160°C under solvent-free conditions, making it suitable for continuous large-scale operations.

This method leverages vanillin as a readily available precursor derived from natural sources.
An alternative industrial route involves the chemical degradation of lignin, a major byproduct of the wood pulping industry, through oxidative breakdown to yield veratraldehyde among other aromatic compounds.

A key example is the metal-free aerobic oxidation method developed by Rahimi et al., which selectively oxidizes secondary benzylic alcohols in β-O-4 lignin model compounds using 4-acetamido-TEMPO as a catalyst with HNO₃ and HCl cocatalysts under 1 atm O₂ at 45°C, producing veratraldehyde in yields up to 92% from relevant models and demonstrating scalability to gram quantities with over 90% selectivity for β-ether units in authentic lignin.

This process enables the valorization of lignin waste, converting it into high-value chemicals via chemoselective C-O bond cleavage followed by retro-aldol fragmentation.
The total production capacity of major manufacturers for veratraldehyde is approximately 2,700 tons per year as of 2023 estimates, predominantly in China (e.g., 1,000 tons from Dongying Yimengsheng Pharmaceutical Co. Ltd., 900 tons from Shandong Holly Pharmaceutical Co. Ltd.), driven by demand in the flavor and fragrance sector.

Cost factors are influenced by sourcing from wood pulping waste streams, which lowers raw material expenses and supports sustainability by utilizing renewable biomass rather than petroleum-based feedstocks.
Environmental considerations emphasize byproduct recycling within the paper industry, where lignin depolymerization not only reduces waste disposal but also minimizes effluent pollution through greener oxidation techniques that avoid heavy metals and harsh reagents.

LABORATORY METHODS of VERATRALDEHYDE:
One common laboratory method for synthesizing veratraldehyde involves the methylation of vanillin using dimethyl sulfate in the presence of a base such as sodium hydroxide.
In a typical procedure, vanillin (1.2 moles) is dissolved in boiling water and treated with an aqueous solution of NaOH, followed by dropwise addition of dimethyl sulfate (2.7 moles total, added in portions) under reflux with stirring, alternating with additional base to maintain alkalinity and acidity cycles for optimal methylation.

The reaction is conducted on a steam bath for approximately 2–3 hours total, yielding crude veratraldehyde as a slightly yellow oil that solidifies upon cooling, with isolated yields of 82–87% after extraction with ether, drying over magnesium sulfate, and distillation under reduced pressure.

A variation employs potassium hydroxide in water with washed dimethyl sulfate, achieving higher yields of 92–95% after filtration and drying of the crystalline product.
Another approach is the oxidation of veratryl alcohol to veratraldehyde using pyridinium chlorochromate (PCC).

This method involves treating veratryl alcohol with ground PCC (typically 1.5–2 equivalents) in dichloromethane at reflux for 2–4 hours, followed by filtration through celite and evaporation of the solvent.
Yields are generally around 70–80%, though specific conditions may vary; for instance, one protocol reports a 62% yield for veratryl alcohol under standard PCC conditions in methylene chloride.

The Swern oxidation provides a milder alternative, utilizing oxalyl chloride, dimethyl sulfoxide, and a base like triethylamine or diisopropylethylamine in dichloromethane at low temperature (−78°C initially, warming to room temperature) over 1–3 hours.
This reagent combination selectively converts the primary alcohol to the aldehyde with yields often exceeding 80% for benzylic substrates like veratryl alcohol, avoiding over-oxidation to carboxylic acids.

Microwave-assisted variants of the Swern oxidation can reduce reaction times to minutes while maintaining high selectivity.
Veratraldehyde can also be prepared via Vilsmeier–Haack formylation of 1,2-dimethoxybenzene (veratrole), an electron-rich arene suitable for electrophilic aromatic substitution at the para position.

The Vilsmeier reagent is generated in situ from N,N-dimethylformamide and phosphorus oxychloride in 1,2-dichloroethane at low temperature (below 15°C), followed by heating to 65°C for reagent formation (5 hours), addition of veratrole, and reflux for 24 hours until veratrole consumption is below 1.5%.

Workup involves quenching with water, extraction, washing to neutral pH, solvent removal, and distillation, affording veratraldehyde in yields greater than 92%.
Across these methods, typical laboratory yields range from 70–90%, with reaction times of 2–6 hours for methylation and oxidation routes, and longer for formylation; purification often entails recrystallization from ethanol to obtain white crystals with melting point around 44–46°C.

CHEMICAL IDENTITY of VERATRALDEHYDE:
NAMES AND SYNONYMS
Veratraldehyde's preferred IUPAC name is 3,4-dimethoxybenzaldehyde.
Veratraldehyde's systematic IUPAC name is 3,4-dimethoxybenzenecarbaldehyde.

Veratraldehyde is known by several other names, including veratric aldehyde, veratral, veratryl aldehyde, veratrum aldehyde, methylvanillin, and vanillin methyl ether.
These synonyms reflect Veratraldehyde's chemical structure and historical associations; for instance, "veratrum aldehyde" and related terms derive from veratric acid, a compound originally isolated from species of the Veratrum plant genus, such as Veratrum album (white hellebore).

The "vanillin" designations highlight Veratraldehyde's close relation to vanillin (4-hydroxy-3-methoxybenzaldehyde) as the O-methylated derivative at the phenolic position.
Known isomers include 2,3-dimethoxybenzaldehyde (ortho-veratraldehyde) and 3,5-dimethoxybenzaldehyde, which differ in the positioning of the methoxy groups on the benzene ring.

SYNTHESIS of VERATRALDEHYDE:
Veratraldehyde is an important organic compound widely used in the fragrance and flavor industry.
Veratraldehyde's synthesis involves the oxidation of a precursor compound, namely vanillin.

One efficient method for the synthesis of veratraldehyde involves the use of potassium dichromate in the presence of Lewis acids under solid phase conditions.
In this process, the reagent potassium dichromate acts as an oxidizing agent, converting the precursor compound into veratraldehyde.
The presence of Lewis acids enhances the efficiency of the reaction by facilitating the oxidation process.

The reaction conditions are carried out under solid phase conditions, which provide better control and yield.
This synthetic method not only allows the conversion of alcohols, acyloins, oximes, and semicarbazones to their corresponding carbonyl compounds but also enables oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers, ethylene acetals, and ketals.

This oxidative deprotection results in the efficient production of carbonyl compounds.
Overall, the use of potassium dichromate in the presence of Lewis acids under solid phase conditions provides a versatile and efficient approach for the synthesis of veratraldehyde, allowing for the transformation of various precursor compounds into this valuable aromatic compound.

MOLECULAR STRUCTURE AND FORMULA of VERATRALDEHYDE:
Veratraldehyde has the molecular formula C₉H₁₀O₃ and a molar mass of 166.176 g·mol⁻¹.
Veratraldehyde's structural formula is (CH₃O)₂C₆H₃CHO, featuring a benzene ring with an aldehyde functional group (-CHO) attached to carbon 1 and two methoxy groups (-OCH₃) positioned at carbons 3 and 4.

This arrangement places the methoxy substituents in ortho and para positions relative to the aldehyde, distinguishing it from the parent compound benzaldehyde (C₆H₅CHO).
The SMILES notation for veratraldehyde is COc1cc(ccc1OC)C=O.

Its IUPAC International Chemical Identifier (InChI) is given by:
InChI=1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3
with the corresponding InChIKey WJUFSDZVCOTFON-UHFFFAOYSA-N.

As a substituted benzaldehyde, veratraldehyde's two ortho/para methoxy groups act as electron-donating substituents, increasing the electron density on the aromatic ring and thereby enhancing its reactivity in electrophilic aromatic substitution and influencing the carbonyl group's susceptibility to nucleophilic attack compared to unsubstituted benzaldehyde.

REACTIVITY PROFILE of VERATRALDEHYDE:
Veratraldehyde is incompatible with strong oxidizing agents and strong bases.
Veratraldehyde is an aldehyde.
Aldehydes are readily oxidized to give carboxylic acids.

PHYSICAL and CHEMICAL PROPERTIES of VERATRALDEHYDE:
Chemical Formula: C9H10O3
Molar Mass: 166.176 g/mol
Appearance: Peach coloured crystals
Density: 1.114 g/mL
Melting Point: 40 to 43 °C
Boiling Point: 281 °C
Solubility in Water: organic solvents
ECHA EINECS - REACH Pre-Reg: 204-373-2
FDA UNII: UI88P68JZD
Nikkaji Web: J9.907D
Beilstein Number: 0473899

MDL: MFCD00003363
CoE Number: 106
XlogP3: 1.50
Molecular Weight: 166.1763
Formula: C9 H10 O3
Appearance: yellow crystalline needles
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 42.00 to 45.00 °C
Boiling Point: 281.00 °C
Congealing Point: 40.00 °C

Acid Value: 2.00 max KOH/g
Vapor Pressure: 0.004000 mmHg
Flash Point: > 110.00 °C
logP (o/w): 1.220
Soluble in: ethyl alcohol, 1 part of 50% alcohol
oils, water, hot water, water
Insoluble in: paraffin oil
Molecular Weight: 166.17 g/mol
XLogP3: 1.5
Hydrogen Bond Donor Count: 0

Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 3
Exact Mass: 166.062994177 Da
Monoisotopic Mass: 166.062994177 Da
Topological Polar Surface Area: 35.5 Å²
Heavy Atom Count: 12
Formal Charge: 0
Complexity: 147
Isotope Atom Count: 0

Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
CBNumber: CB7281578
Molecular Formula: C9H10O3
Molecular Weight: 166.17

MDL Number: MFCD00003363
MOL File: 120-14-9.mol
Melting Point: 40-43 °C
Boiling Point: 281 °C
Density: 1.1708
Vapor Pressure: 0.09Pa
Refractive Index: 1.5260
FEMA: 3109 | VERATRALDEHYDE
Flash Point: >230 °F
Storage Temp: 2-8°C

Solubility: alcohol: freely soluble
Form: Lumps or Fused Solid
Color: White to yellow
Specific Gravity: 1.15
Odor: sweet woody vanilla
Odor Type: creamy
Biological Source: synthetic
Water Solubility: <0.1 g/100 mL
Sensitive: Air Sensitive

Merck: 14,9951
JECFA Number: 877
BRN: 473899
Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
Major Application: flavors and fragrances
Cosmetics Ingredients Functions: PERFUMING
InChI: 1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3
InChIKey: WJUFSDZVCOTFON-UHFFFAOYSA-N
SMILES: [H]C(=O)c1ccc(OC)c(OC)c1
LogP: 0.8

CAS DataBase Reference: 120-14-9
Substances Added to Food (formerly EAFUS): VERATRALDEHYDE
FDA 21 CFR: 172.515
EWG's Food Scores: 1
FDA UNII: UI88P68JZD
NIST Chemistry Reference: Benzaldehyde, 3,4-dimethoxy-
EPA Substance Registry System: Veratraldehyde
UNSPSC Code: 41116107
NACRES: NA.24

CAS: 120-14-9
IUPAC Name: 3,4-dimethoxybenzaldehyde
Molecular Formula: C9H10O3
InChI Key: WJUFSDZVCOTFON-UHFFFAOYSA-N
SMILES: COC1=CC=C(C=O)C=C1OC
Molecular Weight: 166.18 g/mol
Melting Point: 41.0-48.0°C
Form: Flakes
Appearance: White to cream to pale yellow

Assay (GC): ≥98.5%
Free acid (titration): ≤0.5%
Linear Formula: (CH3O)2C6H3CHO
CAS Number: 120-14-9
Molecular Weight: 166.17
Organoleptic: cherry; creamy; woody; sweet; vanilla
Grade: FG, Fragrance grade, Halal, Kosher
Biological Source: synthetic
Agency: follows IFRA guidelines, meets purity specifications of JECFA
Food Allergen: no known allergens

Physical State: crystalline
Color: beige
Odor: No data available
Melting Point: No data available
Boiling Point: 281 °C
Flammability: No data available
Upper/Lower Flammability or Explosive Limits: No data available
Flash Point: 113 °C
Autoignition Temperature: No data available
Decomposition Temperature: No data available
pH: No data available

Viscosity: No data available
Water Solubility: No data available
Partition Coefficient: log Pow: 1.22
Vapor Pressure: No data available
Density: No data available
Relative Density: No data available
Relative Vapor Density: No data available
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: none
Other Safety Information: No data available

FIRST AID MEASURES of VERATRALDEHYDE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of VERATRALDEHYDE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of VERATRALDEHYDE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of VERATRALDEHYDE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of VERATRALDEHYDE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of VERATRALDEHYDE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available